Biggest Longshot Winners in Sports History

In Saturday’s annual Run for the Roses, the Kentucky Derby, Rich Strike pulled off one of the biggest upsets in sports history. The horse wasn’t even in the field until Friday and at 80-1 just before post time Rich Strike became the biggest longshot to win the Kentucky Derby since 1913. 

A record $179 million was bet in the pari-mutuel pool on the 148th Kentucky Derby on Saturday. Rich Strike was the second-biggest longshot in the history of the race. It was 1913 when Donerail won as a 91-1 longshot.

Rich Strike’s victory brings to mind some of the other biggest upsets and longshot winners in the history of sports. Here’s a look at some of the most memorable.

Broadway Joe Calls His Shot

It was Super Bowl III. The Baltimore Colts were a dynasty. They had the game’s best quarterback in Johnny Unitas and the Colts were 18-point favorites against the upstart AFL’s champion, the New York Jets.

The Jets had a brash, young quarterback by the name of Joe Namath. Three days prior to the game, Namath guaranteed a Jets win when he spoke at the Miami Touchdown Club. The game was never really close as the Jets led 16-0 until a late fourth quarter touchdown by the Colts set the final at 16-7. Namath was the game’s MVP without scoring a touchdown.

Buster Does the Unthinkable

Mike Tyson was the heavyweight champion of the world. Buster Douglas (main picture above) was an unknown who was seven years older than Tyson and on his way out of professional boxing. Tyson was 37-0 with 33 knockouts heading into the fight with Douglas. In the eighth round, Tyson knocked Douglas down. What happened next is one for the record books. Douglas rallied and actually knocked out Tyson. He was a 42-1 underdog who was never again relevant after he lost his next bout to Evander Holyfield. 

The Big House Is Stunned

In 2007, the FCS did not yet exist. It was known as Division I-AA back then and Appalachian State was then a member. The Mountaineers, a very good I-AA program at the time, traveled to Ann Arbor to face Michigan, a perennial Big Ten favorite in Week 1 of the 2007 season.

The Wolverines were the fifth-ranked team in the country, but Appalachian State held a 28-17 halftime lead. The game would seesaw back and forth in the fourth quarter when the Mountaineers took a 34-32 lead with just 26 second left in the game. Michigan had a chance to win on a last-second field goal, but Appalachian State blocked it. It was the first-ever win by a I-AA program over a I-A program. The Mounties did it as 33-point underdogs at most sportsbooks.

Greatest Show on Turf

If you haven’t seen American Underdog, you might want to. It’s the story of Rams QB and Hall of Famer Kurt Warner who led his team to a Super Bowl victory in 1999. At the beginning of the season, the Rams were a 300-1 longshot to win the Super Bowl. Starting quarterback Trent Green went down in Week 1 with a season-ending injury.

Enter Warner, a former grocery store bagger and Arena Football quarterback. It is one of the greatest underdog stories of all-time – the Rams rising up as 300-1 longshots and the rise of Warner as one of the NFL’s all-time great quarterbacks.

Olympic Wrestling Upset

If you know nothing of Olympic Greco-Roman wrestling, know this. Russian Alexander Karelin was the best heavyweight wrestler in the world. He hadn’t lost a match in well over a decade (13 years to be exact). At the 2000 Summer Olympic Games, the USA’s Rulon Gardner was in the competition. Gardner had never finished higher than fifth in any international competition. 

In the Greco-Roman heavyweight gold medal match, Gardner was a 2000-1 underdog. To give an idea of just how good Karelin was, he hadn’t even allowed a point to an opponent in six years. Gardner would go on to win 1-0 and capture the gold medal.

Miracle on Ice

There may never be another upset like this one. In 1980, head coach Herb Brooks put together a team of misfit, scruffy college hockey players that would go on to play against the world’s best. Team USA was a 1000-1 longshot to win the gold medal in 1980.

Depending on your age, you have most likely heard veteran sportscaster Al Michaels’ most famous words – “Do you believe in miracles?” Team USA would upset the world’s best team – then the USSR national team – and then would defeat Finland in the gold medal game.